Water → Methyl 1-methylpyrrole-2-carboxylate

HRID 127591

Reaktionsgleichung

Reaktionsgleichung von HRID 127591
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=[O:8].[H-].[Na+].[CH3:12]I.O>CN(C)C=O>[CH3:12][O:8][C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 814531-Methyl-2-pyrrolecarboxylic acid

Produkt 1

HCID 142178Methyl 1-methylpyrrole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

The starting material is prepared as follows: The solution of 1,325 g of 1-methylpyrrole-2-carboxylic acid in 2,400 ml of dimethylformamide is added to the suspension prepared from 568.5 g of 50% sodium hydride in mineral oil and 2,400 ml of dimethylformamide, while stirring under nitrogen and cooling with ice. Thereupon 1,000 ml of dimethylformamide are added, followed by 4,316 g of methyl iodide while stirring and keeping the temperature below 88°. Stirring is continued overnight at room temperature, whereupon the mixture is cooled to 10° and combined with 10,600 ml of water. It is extracted thrice with 5,300 ml of diethyl ether, the extract washed with 5,300 ml of 10% aqueous sodium carbonate and 5,300 ml of water, dried and evaporated, to yield the 1-methylpyrrole-2-carboxylic acid methyl ester as an oil.

Aufarbeitung

  1. customThe starting material is prepared
  2. temperaturecooling with ice
  3. stirringwhile stirring
  4. customthe temperature below 88°
  5. stirringStirring
  6. temperatureis cooled to 10°
  7. extractionIt is extracted thrice with 5,300 ml of diethyl ether
  8. washthe extract washed with 5,300 ml of 10% aqueous sodium carbonate and 5,300 ml of water
  9. customdried
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-71f7cb1a540846a1a57850f6e4f72f48
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256759

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